49845-69-4

Usage

Uses

Used in Pharmaceutical Industry:
(R)-O-Acetylmandelic acid chloride is used as an intermediate in the synthesis of various drugs, leveraging its unique chemical properties and reactivity to facilitate the development and manufacturing of pharmaceutical agents.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-O-Acetylmandelic acid chloride is utilized as a reagent for the preparation of pharmaceutical agents and active ingredients, contributing to the advancement of drug discovery and innovation.
Used in Drug Development:
The specific chemical properties of (R)-O-Acetylmandelic acid chloride make it a valuable tool in drug development, enabling the creation of new and improved pharmaceutical formulations with enhanced efficacy and safety profiles.
Used in Manufacturing Processes:
(R)-O-Acetylmandelic acid chloride plays a crucial role in manufacturing processes, particularly in the production of chiral compounds, where its enantiomeric purity is essential for the desired biological activity and therapeutic effects of the final drug product.

InChI:InChI=1/C10H9ClO3/c1-6(12)7-4-2-3-5-8(7)9(13)10(11)14/h2-5,9,13H,1H3/t9-/m1/s1

Upstream product

• 611-71-2 (R)-Mandelic Acid 
• 75-36-5 acetyl chloride 
• 29071-09-8 2-acetoxy-2-phenylacetic acid 
• 51019-43-3 (R)-(-)-O-acetylmandelic acid 

Downstream Products

• 119154-01-7 N²-D-mandeloyl-L-asparagine 
• 470701-55-4 (R)-Acetoxy-phenyl-acetic acid (R)-1-{(E)-2-[(1R,2S,3R,5S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-vinyl}-hexyl ester 
• 470700-63-1 (R)-Acetoxy-phenyl-acetic acid (S)-1-{(E)-2-[(1S,2R,3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-vinyl}-hexyl ester 
• 470700-62-0 (R)-Acetoxy-phenyl-acetic acid (S)-1-{(E)-2-[(1R,2S,3R,5S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-vinyl}-hexyl ester 
• 470700-61-9 (R)-Acetoxy-phenyl-acetic acid (R)-1-{(E)-2-[(1S,2R,3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-cyclopentyl]-vinyl}-hexyl ester 
• 135984-42-8 (R)-3-(Acetoxy-phenyl-acetyl)-2,2-dimethyl-2,3-dihydrothiazol 
• 130614-76-5 N-isopropyl-O-acetylmandelamide 
• 106863-87-0 Acetic acid (R)-[2-(3,4-dimethoxy-phenyl)-ethylcarbamoyl]-phenyl-methyl ester 
• 116952-35-3 (E)-methyl (R)-3-(2-acetyloxy-2-phenylacetylamino)-2-formyl-2-propenoate 
• 110811-24-0 O-acetyl N-(S)-(1phenylethyl)-(R)-mandelamide 
• 131635-47-7 (R)-(-)-β-acetoxy-α-oxobenzenepropanenitrile 

Relevant academic research and scientific papers

Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum

Six new pyridone alkaloids, named penipyridones A-F (1-6), were isolated from the fermentation broth of an Antarctic moss-derived fungus, Penicillium funiculosum GWT2-24. Their structures were elucidated from extensive NMR and MS data. Although they possess the same major chromophore and some of them presented almost mirror ECD spectra, their absolute configurations were found to be uniformly S, as evidenced by X-ray single-crystal diffraction analysis, stereocontrolled total synthesis, and chemical conversions. TDDFT-ECD calculations of compounds 3 and 6 revealed that subtle conformational changes are responsible for the significantly different ECD curves. None of the compounds were cytotoxic (IC50 > 50 μM), while compounds 1, 2, 5, and 7 elicited lipid-lowering activity in HepG2 hepatocytes.

Design, synthesis and lipid-lowering activities of penipyridone derivatives

On the basis of our earlier discovered natural product penipyridone G with potential lipid-lowering utility, 35 penipyridone derivatives were designed, synthesized and characterized. Based on the oleic acid-induced HepG2 cell lipid accumulation model, compounds 12c, 14, 15f, 15k, 15o, 15p and 16f showed potent lipid-lowering activities among the synthetic compounds at 10 μM. In particular, compounds 4, 15k, 15o showed significant activities on inhibiting lipid accumulation in insulin resistant HepG2 cells, and these three compounds were safe and non-toxic within the concentration range of 400 μM. In comparison, 15o possessed the best lipid-lowering activity. Compared with the vehicle group, the triglyceride inhibition rate of 15o was about 30.2%, and the total cholesterol inhibition rate was about 14.8% at 20 μM, which was equipotent to Simvastatin. Our research indicates that 15o may serve as a promising lead compound for the development of hypolipidemic drugs.

A bifunctional metal–organic framework platform for catalytic applications

DUT-71 (DUT – Dresden University of Technology), a copper paddle wheel based framework, was used as a platform for postsynthetic modification to introduce specific catalytically active sites and to enhance the catalytic activity for fine chemicals product

The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation

A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX?Ru) catalyzed asymmetric hydrogenation of α-aryl keto acids has been successfully developed, affording the corresponding chiral α-aryl α-hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed to several chiral building blocks, biologically active compounds and chiral drugs. (Figure presented.).

Synthetic study of pyrrocidines: First entry to the decahydrofluorene core of pyrrocidines

The first synthesis of decahydrofluorene core 4 of pyrrocidines was accomplished. The cis,trans-fused tricyclic ring system was stereoselectively constructed via Diels-Alder reaction using two Danishefsky dienes.

Second generation of fucose-based DC-SIGN ligands: Affinity improvement and specificity versus Langerin

DC-SIGN and Langerin are two C-type lectins involved in the initial steps of HIV infections: the former acts as a viral attachment factor and facilitates viral invasion of the immune system, the latter has a protective effect. Potential antiviral compounds targeted against DC-SIGN were synthesized using a common fucosylamide anchor. Their DC-SIGN affinity was tested by SPR and found to be similar to that of the natural ligand Lewis-X (LeX). The compounds were also found to be selective for DC-SIGN and to interact only weakly with Langerin. These molecules are potentially useful therapeutic tools against sexually transmitted HIV infection.

New chiral ligands derived from mandelic acid: Synthesis and application in the asymmetric phenyl transfer reaction to an aromatic aldehyde

Starting from inexpensive enantiopure (R)- and (S)-mandelic acid, a range of α-hydroxy-2-oxazolines has been prepared. The synthesis involves the condensation of the acid chloride with a vicinal amino alcohol, followed by intramolecular cyclization to form the oxazoline ring. The resulting compounds have been used as ligands in the asymmetric phenyl transfer reaction to 4-chlorobenzaldehyde, employing a mixture of triphenylborane and diethylzinc as the phenyl source. Good yields (up to 76%) and moderate enantioselectivities (up to 35%) have been achieved.

STEREOCHIMIE DE LA REDUCTION ELECTROCHIMIQUE D'α-CETOAMIDES OPTIQUEMENT ACTIVES I. ELECTROREDUCTION DE LA S(-) N-(α-METHYLBENZYL)BENZOYLFORMAMIDE

Electrochemical reduction of the title compound has been investigated in hydro-alcoholic medium, at a mercury cathode.Polarographic study shows adsorption of the substrate in very acidic medium (pH 5.5.Controlled potential electrolyses give the corresponding mandelamide in a quasi-quantitative yield; titration of the mixture of the two epimers is achieved by proton NMR at 300 MHz.In very acidic medium, preferential formation of the RS mandelamide is observed (higher optical yield:12.5percent).On the contrary, SS mandelamide is generally the main stereoisomerin acetic or ammoniacal buffer; however, when electroreductions are carried out at very cathodic potentials, again preferential formation of the RS epimer is observed.Stereochemistry of the reduction is explained taking into account conformations of the starting molecule and protonation of the carbanion resulting from a 2 electron reduction.

The Preparation and Absolute Configuration of the Optically Active Forms of the Diastereoisomers of 2-(1-Phenylethyl)amino-1-phenylethanol and Their Use as Chiral Auxiliaries in the Asymmetric Reduction of Acetophenone with Modified Lithium Aluminium Hydrides

(1S,2S)-(-)-2-(1-Phenylethyl)amino-1-phenylethanol (4b) (α-form) and the (1S,2R)-(+)-diastereoisomer (4f) (β-form) were prepared by lithium aluminium hydride reduction of the optically active amides derived from the appropriate mandelic acids and 1-phenylethylamines.The preparative methods give the absolute stereochemistry.The aminoethanols (4) were used along with the lower alcohols to prepare chirally modified lithium aluminium hydrides which were in turn used to reduce acetophenone.The optical yields varied, giving at best, under low temperature conditions and use of a 25 percent optical yield.